Casey Dienel is in Portsmouth, New Hampshire, and she’s about to sing her Massachusetts song. It’s a Monday night at the Red Door — a living-room-style martini bar with crimson walls, snug couches, and candlelight — and the 21-year-old Scituate native is settled behind a silver Roland keyboard in a white blouse and stockinged feet, about to play "Frankie and Annette," a Masshole revision of "Jack and Diane" with a Bonnie-and-Clyde twist ("It all started at a Red Sox ballgame"). The cutely chatty five-foot-tall blonde had pulled out "Frankie and Annette" a week ago at a tour stop in Athens, Ohio, when she’d heard that Jonathan Richman recently played the same room.

But tonight the former New England Conservatory student doesn’t mention any of this and instead introduces her forthcoming number to the packed house as "a song about two people who got fed up with working shitty jobs." Dienel has worked sundry "shitty jobs" — slicing exotic cheese in the South End, slapping together sandwiches at Espresso Royale. That last gig inspired the Jamaica Plain resident to scribble a song called "Rules for Survival," about how much she hates deli meat. "Rules" didn’t end up on Wind-Up Canary, Dienel’s first full-length on Hush Records, the Oregon indie label that first supported the Decemberists. But other songs with adorably eccentric subjects did. Like "Doctor Monroe," a show-tune-y, drum-brushed opener about a deranged drunk she once met on a train in Europe who communicates with the sixth dimension through public urinals and smells like turpentine. Or the gracefully sad ode to a defeatist friend who, Dienel recalls, "was just being a total dick and trying to write everybody out." That one’s called "Fat Old Man."

Wind-Up Canary is full of these idiosyncratic turns, such as autumn personified as a wintery beggar "jangling a coffee cup outside Store 24," in the wanderlust-bitten, harmonica-soothed "Cabin Fever." Throughout the record, Dienel’s lyrics are literary constructions decked with richly descriptive props: Polaroids, Playboy magazines, barrettes, strawberry wine, baked Alaska, needlepoint, a Folgers can, a Cracker Jack box. She also manages to slip euphemistic one-liners such as "I called in sick to the bathtub today" into a song with the memorable chorus "Oh you held me like a tundra" — without seeming overwrought.

Even Dienel’s online biography reads more like the first sentence of a novel than typical PR drivel: "I grew up in a small seaside village with the cockleshells and sand mites." She started playing piano at the age of four. "This might sound like Little Einstein, but I remember looking at the piano and I could hear songs in my head," she recalls. Her father’s a guitarist, so inevitably "my parents kind of hooked me up to the good stuff, like Carole King and Joni Mitchell." In school, she couldn’t deal with pecking out children’s’ standards on the keyboard. "When you’re a kid and you’re exposed to [Joni Mitchell] and someone gives you a song called ‘Three Hungry Snowmen,’ you’re just like, ‘Give me a break.’"

Throughout adolescence, Dienel was shy. Even worse, "I was really gawky too. I didn’t have boobs until I was, like, 18." So music "was a good way to make friends."

She has plenty of friends now. Fellow ivory-banger Amanda Palmer from the Dresden Dolls is a fan. For more than a year, Dienel has been a sometime member of the Newburyport orchestral-folk collective Tiger Saw. And Dienel’s boyfriend is Nat Baldwin, a Portsmouth-based vocalist and upright-bass player who opened for her at the Red Door.

Dienel is moving to Brooklyn in 2006. But today she’s still in New England, finishing up her set with Wind-Up Canary’s closer, "The La La Song." Cajoling nearly everyone into a sing-along of la-la-la’s, she bounds up from the keyboard and runs around the room. As Dienel hopscotches among the square ottomans, waving her arms for everyone to continue, one woman in a ponytail cuddled up with a goateed guy in a front-row couch mouths to her companion, "I like her."